Imagine: Dean woke up as a female
by waywarddemons
Summary: Dean wakes up as a female and has a little too much fun exploring his new body.
Thanks to the bunker not having windows, Dean had completely no idea what time it was when he finally stirred awake. He rolled to his back, laying there for a moment before forcing himself to his feet. He drug his feet against the concrete as he made his way to the kitchen. Scraping his slippers with each step.

Thankfully Sam was on another all week long cram session so there was plenty of coffee made and ready for Dean to drink. Dean leaned against the table, sipping on his coffee with his eyes closed as he still tried to bring himself awake.

Before Dean knew it he had been flipped around and his face was pressing into the table. "What the hell man?" Dean asked. He attempted to shake free of his brother's grasp, but Sam only pushed him harder. He twisted his arm back tighter, pressing his knee into the small of Dean's back. "Come on man, get off me."

"Who are you?" Sam practically yelled and Dean could feel the cold of his brother's gun through his t-shirt being pressed into his shoulder. "Who are you?" He yelled again, Dean could hear Sam cock the gun.

Dean remained still under his brother, heart racing as he tried to understand what was going on. "Sam, it's me. Dean."

"Very funny." But Sam's grip loosened slightly, enough for Dean to get the upper hand. Dean smacked the gun away listening to it slide across the floor. He had managed to now be the one pressing Sam into the table, but he tapped his shoulder and took a step back.

"What the hell Sammy?" Dean asked. "We don't need training this early."

Sam stood, brushing the imaginary dust from his shirt. "Stop playing and tell me who you are!"

Dean looked up at his brother, more than normal and suddenly felt weird. "Sammy?" Dean asked, watching the look of sheer confusion coming across his brother's face. Suddenly, water came splashing against Deans face. "Come on, why the hell would you think I'm a demon?"

"Uh," Sam rubbed at the back of his neck, "Tell me something only Dean would know." He crossed his hands over his chest.

Dean scoffed, "Where do I start?" Dean thought about it, coming up with a few different good ideas on how to embarrass the hell out of his brother. He thought about when Sam was little, or his awkward teenage years, or even a few recent things. "Okay. Your Netflix shows you previously watched Dr. Sexy MD." Dean wagged his eye brows.

"So what? You like that show too!" Sam defended, swinging his large arm in the air and pointing at his younger brother.

Dean stopped his laughing, Sam had always given him shit for being obsessed with that show, so to return the favor was nice, until it blew up on his face again. "Yeah, but-"

"Okay, okay." Sam raised his hands to stop his brother from continuing. "So I take it you haven't looked in a mirror lately?"

"No, unlike some people I don't need to constantly fix my hair." Dean rolled his eyes.

"You should uh- yeah, you need to see this for yourself." Sam gripped his brothers arm and pulled him to the nearest mirror in the bunker.

There Dean stood, looking in the mirror but not seeing himself. He raised a hand to pet at the long hair cascading down the sides of his face. He leaned in closer, seeing the same marks he himself had, on a new female face. He looked back at Sam who was stifling a laugh the best he could.

"What the hell man?" Dean asked.

"I don't know." Sam drank in his brother's new form, seeing him, her, for the first time.

"No really? What the hell?" Dean looked in the mirror again, but quickly took off towards the bathroom where he could get a better view of himself. "Why don't we have any full length mirrors?!" He yelled, dragging Sam to the sound of his voice.

"We do; we just never have to use them!" Sam called, slowly making his way towards the shower room. He could hear Dean shuffling away in there, but it wasn't until he heard a crash that he picked up the pace.

Dean lay on the ground, his oversized shirt lifted up over his head exposing his bare naked chest. Sam averted his glance, not before he could see the brown perky nipples glaring up at him. "Come on Dean. I don't want to see that."

Dean picked himself off the ground, raising his shirt up again, this time he could see for himself. "Yeah right! This is probably the closest you've been to a pair of tits in how long?" Dean smirked, jumping up and down in front of the mirror and watching the way his new body moved.

"Yeah," Sam couldn't help but look again, watching Dean's breasts bounce. "But they're my brothers, sisters, man I don't know but I don't think you should be flashing them to me." Sam placed a hand over his eyes as he walked into the room and pulled Dean's shirt down. It fully engulfed him, his small frame disappearing behind the large black t-shirt.

"I'm not." Dean ripped out of Sam's grasp. He raised his shirt again, this time only showing his stomach. "I'm exploring my own body. You joined me in here."

"You're not curious how this happened?" Sam leaned against the counter, watching as Dean dragged his soft hands around his torso.

"Of course I am Sammy, but look, I have a girl body. This is like- the best thing ever."

"Glad you're so excited. But maybe you could take a break for a moment and, I don't know, help me figure out what happened?"

"You're such a party pooper. Yeah alright." Dean sulked out of the bathroom, Sam close behind.

They entered the library, where Dean kicked up his slipper ridden feet on the table and waited for Sam to join him. "So what lore books to we look to for this freaky Friday gender swap?" Dean watched as his younger brother made his way to the shelves, running his long fingers over the spines of books as he struggled to find one that he could use.

Sam hit his head against the shelves, "I don't know. We could call Cas? Or Crowley?" Sam turned, catching Dean rubbing his hands against his newly smooth legs.

"NO!" Dean yelled. "Crowley will never let me live this down, and the fluffy angel…" Dean leaned back in his seat, sighing at the thought of Cas showing up in the bunker right now. Dean reached forward, gripping a beer bottle left behind from who knows when and raising it to his lips.

Sam scoffed, "What don't want him to see you like this?" Sam joined Dean at the table, sitting across from him. Dean set the newly empty bottle down, and looked up at his brother.

"You're finally the one with short hair." Dean joked. "You're right, Cas probably knows how to fix this." He ran a hand down his face. "Call him." Dean stood, making his way to the kitchen for another drink, he grabbed a few, needing to feel slightly buzzed so he could deal with all of this.

He could hear Sam on the phone, hear him explaining to Cas that there was a situation that needed his assistance. Dean rolled his eyes, looking down at his body once more. He shrugged, strangely satisfied with the way he looked now.

Sam hung up his phone as Dean entered the room. Dean struggled to twist off the bottle lid, grunting and growing frustrated before slamming the thing down. Sam chuckled as he reached for it, opening it easily and sliding it to Dean.

"I am not going to say thank you." Dean said, slinking back the cold liquid. Sam sat staring, watching as the female before him moved the same way his brother would have. "Stop staring, it makes me feel all weird."

"How does… how does it feel?" Sam finally asked.

"Soft."

Sam laughed, "Soft? That's all you got?"

Dean stood, making his way to his brother's side of the table. "Dude, feel. Soft." He gripped Sam's hard callused hand in his and planted it on his hip. Sam hesitated to move, but with Dean's force his fingers drug against him. Dean felt the scratch of Sam's skin on his and felt a warm sensation fill him.

Dean coughed and took a step back, dropping his brothers hand and replacing it with his beer. "Yeah, soft." Sam said, clearing his throat and sitting up straight.

The bunker door creaked open and Dean chugged his beer, wishing it was something stronger. He wasn't so embarrassed around his own brother, but something about being around anyone else made Dean feel odd.

"I don't understand why you couldn't explain to me over the phone why I needed to join you Sam. I do have things to do." Castiel joined them, his hands resting next to his sides in his trench coat covered arms.

Cas looked at Dean, unaware of who he was. He looked back at Sam, a flash of something along the lines of anger in his eyes. "Sam, where is Dean? Who is this? Why does she look so familiar?"

Dean handed his brother another beer bottle, silently asking him to open it. Sam did so, his eyes not leaving Castiel's as he tried to think of how to put into words what had happened. Dean chugged his drink in one long drink and slammed the bottle down.

"That is not very lady like of you." Castiel said, watching the bottle almost fall. He stood close to Dean now, looking at him in a way that made Dean feel uneasy, uncomfortable, and like he was suddenly under a microscope.

Dean cleared his throat. "Cas, its me. Dean."

"Yes, I see it. Why are you a female?" Cas took a step back, looking over Dean's new body with slow eyes. As if he were memorizing this new person all over again. Though, it was starting to become painfully obvious it was Dean. The way he stood, his legs slightly bowed, his pouty lips, green eyes.

Sam cleared his throat, "We were kinda hoping you could tell us Cas."

"Me? How would I know what happened?" Cas finally pried his eyes off of Dean, turning to the larger younger brother who still remained sitting. Dean finally felt like he could breathe, like he was no longer feeling the weight of Castiel's eyes on him.

Sam cocked his head to the left, "Cause you're an angel?"Castiel shook his head at Sam's words, placing two flat hands on the table. "Do you know what does have this kind of power?" Sam asked, hopeful that Castiel could shed even a small light on what was going on.

"Maybe." Castiel stood, turning back to Dean. "Dean, I don't think you should…." He started with all seriousness. Sam peaked around his trench coat wearing friend to see Dean with one breast exposed. He tugged and pulled at his nipple, seeing how far he could stretch it out before letting go and watching it bounce back to shape. His left nipple was a hard nub now, and a childish smile spread across Dean's face.

"Oh come on, not you too. Can't a girl just feel herself up a little?" Dean watched as both men shifted uncomfortably before letting the fabric of his shirt drop. "So no one has any idea how to put me back?"

Castiel cleared his throat and watched Dean sink into his chair, without hesitation Sam opened the last beer you brought into the room and slid it to you. Both men stared at Dean, watching as he drank the beer, his lips pressing into the glass. After he set it down he darted his tongue across his lips to capture what might have been lingering.

"What's it feel like?" Sam blurted out without thinking.

This caught Dean off guard. He looked at Sam, seeing the familiar twinkle in his eye when he was around girls. Attractive girls. He shifted his gaze to Castiel, who like earlier was watching in intently, but it was different, something about it…

"Its uh, different. I mean the same kind of. Except every time I move, this shirt scrapes against my nipples and makes them all hard. And I feel all airy between my legs." Dean rambled on, but Sam and Castiel were entranced with the fact that they could still visibly see Dean's erect nipples. "How do you deal with all this damn hair; I mean its fuckin' everywhere."

This got a laugh from Sam, who ran a hand through his own locks. "You get used to it."

"I want to cut it all off." Dean copied Sam's motions, running a hand through his hair and pushing it out of his face. "I said stop stairing!" Dean yelled, feeling Sam's eyes still on him.

"Sorry. Its just. Your kinda hot." Sam said, once more blurting out the words before his mind could process them. "I mean, I knew you were a good lookin guy, but…"

"Stop it Sammy." Dean blushed. Sure even he knew that he was a good lookin guy, hell how else could he get as much action as he got? But hearing his own brother say those words made Dean's skin feel flush.

"He's right." Castiel added. And as if Dean needed more reassurance, Castiel stood up straight, revealing the rather large tightness happening in his slacks.

"Cas!" Dean said, his face turning an all new shade of red. "Contain yourself man! Its still me in here."

"I know, but watching you play with your breasts made it happen." He bent down again, hiding the hardness from view.

Dean gave a sly grin, a new found confidence washing over him. He slowly pealed up his shirt, showing his pale freckled skin to the grown man until he reached his breasts. "You mean when I did this?" Dean pinched at his already hardened nipple. Rolling it between his forefinger and thumb. Castiel swallowed the lump forming in his throat and bent over more, his legs crossing under him.

Dean pulled at the nipple, stretching it out and letting it go as he had earlier. He moved to the other, feeling like he was neglecting it. Repeating his process, eyes never leaving Castiel's. It wasn't until Sam cleared his throat that Dean even remembered he was in the room.

Sam could clearly see everything happening before him. and despite wanting to not watch, he couldn't help but keep his eyes glued on Dean's rather large chest. Sam could feel himself growing hard in his jeans and using the palm of his hand he pressed it firmly into his thigh to hide it.

Dean couldn't help the small moan that left his lips after gripping both nipples in his fingers. He used both hands now, pinching, rolling, twisting. And where he normally felt himself growing harder, he felt wet and slick.

He kept looking back from Castiel to Sam, watching them squirm as he continued to play. Dean licked his lips and dragged his hands down his torso. Sam no longer could see what Dean was doing, but he had a pretty vivid imagination as to where Dean's hands were going. Castiel though, he could see Dean's slim fingers slip into the hem of Dean's boxer briefs.

"Dean come on!" Sam yelled, slamming a hand on the table and breaking everyone's thoughts. Dean jumped, removing his hands and placing them in the air.

"Don't get all pissy Sammy. You can watch too." Dean winked. He wasn't sure what was coming over him, but he wasn't about to abandon it now that this heat was rising from between his thighs.

"Dean you're my brother. And the last thing I want to do is watch you play with yourself." Sam's words sounded sincere, but both Dean and Castiel could see his eyes and body telling a different story. Sam's eyes were dark with desire, need, and want. His body was rigid as he continued to hide his thick hard cock.

"Oh come on Sam. You haven't been this close to a pussy in months. Live a little. Who knows how long I'll be like this anyway." Dean stood, and proceeded to climb over the table towards Sam. "Come on Sammy, you know you want to explore this body." Dean hovered inches from Sam's mouth, his breath smelling of coffee and beer.

Sam hesitated, looking at his brother's eyes and darting to his lips. Just as Dean was going to climb off the table, just as he was about to give up, Sam's large hand snaked around him and pulled him into a kiss. Sam's fingers twisted into Dean's long hair, pulling just enough to force Dean's breathing to hitch.

Sam was the first to beg for entrane into Dean's mouth, his tongue liking his bottom lip, ready to dive into Dean's new mouth. Dean allowed his brother access, and when Sam's tongue dived in, Dean couldn't help but feel the need to be closer. He needed more.

Castiel groaned next to them, reminding them that he was there and suffering. Sam allowed Dean to turn his head to the other man, and the fuzzy look on Dean's face almost had Castiel cumming in his jeans. "Don't worry baby. You'll get a turn."

Sam let go of Dean's hair and leaned back in his chair, his mind was allowing him to think again, think of the fact that Dean's lips were just pressed to his. That he had enjoyed kissing Dean a lot more than he wanted to admit, and that he wanted more.

Dean rose to his knees, still on the table. He reached for the hem of his shirt and raised it above his head, removing it completely and throwing it back on his chair. Castiel didn't waist another second, not wanting to be on standby any longer. He engulfed Dean's nipple into his mouth, tongue flicking over the hard nub. Dean leaned his head back, his hair tickling him. Castiel hummed with Dean's nipple in his mouth, pressing his shaft into the side of the table to contain himself.

Sam joined, taking Dean's other nipple in his own mouth. Dean felt his skin tingle, felt the moans rising in his throat and leaving his lips. He ran his hands through both men's hair, encouraging them with their actions. Dean had had his nipples played with before, and had enjoyed it, but nothing, absolutely nothing felt like this.

Sam's callused hand scrapped at his back, pushing Dean against his head harder. Castiel's soft hand cupped his ass, squeezing it every few moments. Dean's hands left his friends, and made their way back into his boxers. He felt the warm wetness of his lips, dragging a finger across them and his clit. His body shivered, and he brought his newly slicked fingers to his mouth.

"Damn I taste good." He said.

Castiel nibbled on his nip before pulling away. His blue eyes were as dark as Sam's as he removed his hand from Dean's ass and have him a kiss. He could taste him as his tongue forced itself against Deans. A deep groan left him and filled Dean.

Sam had stopped, taking a moment to watch Castiel and Dean kissing. His hands raked over Dean's new body, feeling every inch of the exposed skin he could. He toyed with the idea of entering the boxers, his fingers dragging playfully along the top of them.

Dean stopped the kiss, his hand gripping Sam's and helping it plunge into his boxers. Sam's fingers instantly found Dean's wetness, and with a gentle touch he rubbed a few small circles against Dean's clit.

Dean moaned, loudly and ground his hips against his brothers touch. "Yes Sammy. Right there."

Castiel had pulled out his thick cock, pumping it a few times as he heard Dean moan. The sound was wonderful, and every time a little whimper left Dean's mouth he could feel his orgasm rising inside of him. Dean opened his eyes long enough to see a fully dressed Castiel jerking himself.

Sam removed his hand as Dean slipped out of the boxers, kicking them so they joined the shirt he wore previously. He kneeled there naked for a moment, watching Castiel with his cock in his hands. Dean bent on all fours, his hands against the cool table. He turned so Sam now got a full view of the full lips that were now Dean's. Dean reached for Castiel, his small hands gripping the man's cock and pulling him to him.

With a little giggle Dean opened his mouth, pulling Castiel to the tip of his tongue. He slapped Castiel's head against it, tasting the salty precum that had oozed from it. He looked up, seeing Castiel sucking on his own lower lip as Dean dragged his tongue across his shaft. Castiel broke first, closing his eyes and leaning his head back as an animalistic growl left him.

Dean inched the cock into his mouth slowly. Unfamiliar with the small girth of his new mouth. It wasn't until he felt Sam's mouth against his aching pussy that he swallowed most of Castiel. Castiel's hands gripped Dean's head, helping him find the right rhythm and speed. Which was helpful since Dean no longer felt in control of his body. With Sam's tongue lapping up the wetness he could, and darting in and out of the tight hole of Dean's, Dean felt like he was on drugs. His body hummed with horniness.

Castiel and Sam must have shared a look, because suddenly they both sped up, working Dean's holes quickly. Sam plunged finger into Dean's tight pussy and Dean moaned around Castiel's cock. Castiel groaned and pulled his cock from Dean's lips. "I'm going to.." He breathed.

"Switch me." Sam said, rising to his feet and dropping his pants to the ground. Dean breathed in heavy steps as the men switched positions. He could feel a whole new level of wetness dripping from his pussy and hoped that he hadn't already came.

"Its beautiful." Cas said slapping a hand against Dean's ass.

Sam lined his cock up with Deans mouth, "It is isn't it? Wait till you get a taste. Best damn pussy I've ever had."

Dean shook at his brother's words, or maybe it was that Castiel had shown his other ass cheek the same affection as the other with a firm hand slapping across it. Dean moaned, and just as he was about to clench his teeth shut, Sam was plunging his cock into his mouth.

Dean sucked, more aware of his movements against his brother's cock as he now had free reign to do as he pleased. Dean recalled a few of the porn videos he had watched and tried to recreate them.

Cas worked slower, his fingers wanting to feel every inch of Dean's new lower half. So when his finger finally pressed against Dean's already swollen clit Dean could have sworn he came. Castiel spread Dean open wide for himself, and gave one small lick against the length of it. Dean's legs shook in anticipation.

"It is delicious." Cas hummed, his mouth now working wonders against Dean. Sam started helping Dean, pumping himself in and out of his brother's wet hot mouth. He was much longer and thicker than Casitel, but he pushed himself farther down Dean's throat, and Dean gagged. But this didn't stop Sam, no, he wanted more. His large hands held Dean's head still as he rocked back and forth into his mouth, pumping it deep and quick.

Spit dripped from Dean's mouth and fell down Sam's length. Castiel slipped a finger into Dean, his mouth moving up along the slit and licking Dean's asshole. Castiel pumped his finger matching Sam's speed, while his tongue slipped in and out of Dean's asshole.

Screams left Deans mouth as his first orgasm rippled through him, his legs shook and everything clenched. Dean's vision blurred, turning white as he released himself against Castiel's finger. Sam pulled away, watching the strings of saliva link him to Dean's mouth. "I-I came." Dean managed to say.

Castiel removed his finger and rose to his feet. "Taste this." He said to Sam, how didn't hesitate to suck on Castiel's soaking finger. Castiel stuck his other inside of Dean, tasting the sweet juices for himself.

"Fucking delicious." Sam moaned. His cock twitching in need to release. "How should we cum?" He asked Castiel.

"Each get a hole? I'd love to feel this asshole." As he spoke he pressed a firm finger against it.

Sam laughed. "I got an idea." He helped Dean back to his knees, and the dazed look on Dean's face only made him more excited to have him cumming over and over again. He pulled Dean off the table by his ass, and Dean quickly grasped at his brother's torso to keep from falling.

"What? What are we?" Dean asked, but no one answered. Casitel came from behind him, and Dean felt his lips against his neck. Cas pressed the head of his cock against Deans soaking pussy, using the juices to lube his cock enough to enter Dean's ass.

The pressure hurt, and Dean hissed as Castiel's cock stretched him. "Relax, it will only hurt more if you don't." Castiel whispered, through his own hisses of pleasure. Dean was tight, so tight it was almost impossible for Casitel not to cum instantly.

Dean did as he was told, relaxing himself until he felt Castiel's hips against his ass. "Cas." Dean moaned. And then came Sam, who wasted no time plunging his cock into Deans pussy. "Sam!" Dean screamed, but nothing compared to this feeling.

Sam lifted Dean up and down along the both of them, and Dean didn't hold back anything. The small, the large, and the loud moans leaving his mouth as he being filled in each hole. They started slow, both men needing to contain themselves against Dean's tightness. But as he loosened up they both were able tospeed up.

"Im gunna cum!" Dean screamed as yet another orgasm ripped through his body. He wanted to collapse, he didn't think he had it in him to continue even as they didn't stop. The deep grunts and moans leaving the both of them, the sweat slicking them all against one another was driving Dean insane as he held on to both of them around their necks.

Again Dean came, at least another two times before he felt a hot seed filling his asshole and dripping out of him. Castiel's cock throbbed inside of him as Sam continued to work Dean against them. Castiel pulled out, dropping into the chair next to him as he watched his cum drip out of Deans ass. He watched, his cock completely flaccid as Sam all but threw Dean's back against the table. Sam lifted Dean's legs to his chest, and pounded as deep and hard as he could into his brother's pussy. "I'm- I'm!" Dean screamed his body shaking and convulsing as yet another orgasm ripped throughout his body.

Sam wasn't done, he felt Dean clench around him, but he continued to quicken his pace, sliding in and out of Dean in quick motions. Finally. Sam felt his orgasm rising, he watched Dean's withering body under him, gipped Dean's hips tight and with one deep final plunge his release was met.

Sam collapsed on top of his brother for a moment, letting his hot sticky cum fill Dean's pussy before slipping out and falling into his own chair. He panted, wiping his sweaty wet hair from his face. Dean lay there, unable to move. His legs were twitching, his breathing heavy, and his head light. He could hear Castiel and Sam shuffling around, but it wasn't until Sam was carrying him bridal style that Dean even bothered to move or pay attention.

"Where are you taking me?" Dean asked, his breath finally normal now. He was tired, a whole new level of tired he had never felt. He'd had his fair share of sex marathons, but nothing, absolutely nothing compared to how he felt right now. He could feel the bruises forming on his hips from Sam's grasp on him, and between his thighs where he was repeatedly thrust against.

Warm water cascaded down Deans body, Sam had placed him gently on the ground in the shower and let the water wash over Dean's sweaty body. Castiel and Sam watched as his eyes fluttered, and he soon fell fast asleep.

XXX

Dean awoke with a start, his hands jumping to his chest quickly to feel what was there. He sighed, both from excitement that he was back to his normal male body, and in sadness, because he had wanted to feel as used and tired as he had in his dream. He made his way out of his room, roaming the halls of the bunker until he could hear Castiel's deep gravelly voice and Sam's talking in the library.

"Morning guys." Dean said, joining them and sitting next to Castiel. He tried hard not to erase the thought of him playing with himself here before, in his dream. But his own cock twitched at the thought.

"Dude, its like 6pm." Sam said, flashing his watch to his brother.

Dean leaned forward, looking at the time before leaning back and scoffing. "Man, I must have drank too much or somethin'" he scratched at his neck, suddenly embarrassed that he had slept for so long. "What you doin' here Cas?" He asked, looking over at his fethered friend.

"Uh, Sam needed my help with something. But we got it all cleared up and were just talking."

"Oh yeah? Didn't think to wake me to help you?" Dean said, drumming his fingers against the table. The table he had previously just been fucked on. It was cold, just like it had been in his dream, and once again his cock twitched at the thought.

"Oh I don't think I could have if I tired." Sam laughed. And Castiel shared a look with him before they both turned back to Dean. "But it's okay. Cas, uh, helped me solve a case and were both pretty wore out."

Dean nodded in acceptance. "Yeah, I'll probably just uh, find something to do." Dean said, shoving his hand in his pocket and pulling out his phone. At first he thought he saw something in the reflection, wishful thinking he supposed. But when he turned on his camera app to make sure, and saw the small markings of a hickey on his neck his heart started racing. "What is this?" He asked, looking back and forth between the two men next to him.

"Wow, Cas said you wouldn't remember. But I didn't think that was possible to forget." Sam said, leaning back in his chair.


End file.
